Rosenmund reduction 3252738 221674570 2008-06-25T15:51:21Z Chem-awb 4806773 [[Category:Name reactions]] using [[Project:AutoWikiBrowser|AWB]] The '''Rosenmund reduction''' is a [[chemical reaction]] that [[redox|reduces]] an [[acid halide]] to an [[aldehyde]] using [[hydrogen|hydrogen gas]] over [[palladium-on-carbon]] [[catalyst poisoning|poisoned]] with [[barium sulfate]].<ref>{{cite journal | author = [[Karl Wilhelm Rosenmund|Rosenmund, K. W.]] | title = Über eine neue Methode zur Darstellung von Aldehyden. 1. Mitteilung | journal = [[Chemische Berichte]] | year = 1918 | volume = 51 | pages = 585–593 | doi = 10.1002/cber.19180510170}}</ref><ref>{{cite journal | author = [[Karl Wilhelm Rosenmund|Rosenmund, K. W.]], Zetzsche, F. | title = Über die Beeinflussung der Wirksamkeit von Katalysatoren, 1. bis 5. | journal = [[Chemische Berichte]] | year = 1921 | volume = 54 | pages = 425–437; 638–647; 1092–1098; 2033–2037; 2038–2042 | doi = }}</ref><ref>Mosettig, E.; Mozingo, R. ''Org. React.'' '''1948''', ''4'', 362. (Review)</ref> The reaction was named after [[Karl Wilhelm Rosenmund]]. [[Image:Rosenmund_Reduction_Scheme.png|center|300px|The Rosenmund reduction]] The catalyst must be poisoned because otherwise the catalyst is too active and will reduce the acid chloride to a primary [[alcohol]]. [[Diisobutylaluminium hydride]] (DIBALH) can also reduce acid chlorides to aldehydes. ==See also== * [[Grundmann aldehyde synthesis]] ==References== <references/> ==Further reading== * {{OrgSynth | collvol = 6 | collvolpages = 1007 | prep = cv6p1007 | title = Aldehydes from Acid Chlorides by modified Rosenmund Reduction: 3,4,5-Trimethoxybenzaldehyde | author = A. I. Rachlin, H. Gurien, and D. P. Wagner | year = 1988}} * {{cite journal | author = Saytzeff, M. | title = Ueber die Einwirkung des vom Palladium absorbirten Wasserstoffes auf einige organische Verbindungen | year = 1873 | journal = [[Journal für Praktische Chemie]] | volume = 6 | issue = 1 | pages = 128–135 | doi = 10.1002/prac.18730060111}} [[Category:Organic redox reactions]] [[de:Rosenmund-Reduktion]] [[ja:ローゼンムント還元]] [[ru:Реакция Розенмунда — Зайцева]] [[Category:Name reactions]]